Synthesis, toxicities and cell proliferation inhibition of CO-releasing molecules containing cobalt

Gong, Yaguo; Zhang, Taofeng; Liu, Huapeng; Zheng, Yawen; Li, Na; Zhao, Quanyi; Chen, Yonglin; Liu, Bin

doi:10.1007/s11243-015-9931-4

Cited by 17 publications

(18 citation statements)

References 30 publications

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“…The orientation of the ester substituent as well as its size influence the packing mode of ester derivatives of GE. In crystal structures (1)-(3) (Beseda et al, 2010;Gong et al, 2015) the ester groups show an alternative orientation to that found in (4)-(6). These two orientations are related by approximately 180 rotation about the C-C single bond between the ester group and the triterpene skeleton (Table 4).…”

Section: Ester Derivatives Of Ge -Comparison Of Crystal Packingmentioning

confidence: 78%

“…Our survey of the CSD gave three esters of GE varying in size and nature of the oxy substituents (Scheme 1). Compounds (1) (Beseda et al, 2010) and (2) (Gong et al, 2015) with large substituents reveal the layered assembly of molecules, whereas in the methyl ester of GE (3) (Beseda et al, 2010), a different arrangement is found that has not been observed in the crystal structures of GA, CBXH 2 and GE.…”

Section: Introductionmentioning

confidence: 84%

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Self-assembly modes of glycyrrhetinic acid esters in view of the crystal packing of related triterpene molecules

Langer

Wicher

Szczołko

et al. 2016

Acta Crystallogr B Struct Sci Cryst Eng Mater

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The crystal structures of three ester derivatives of glycyrrhetinic acid (GE) are reported. X-ray crystallography revealed that despite differences in the size of the ester substituents (ethyl, isopropyl and 2-morpholinoethyl) the scheme of molecular self-assembly is similar in all three cases but differs significantly from that observed in other known GE esters. According to our analysis, the two basic patterns of self-assembly of GE esters observed in their unsolvated crystals correspond to two distinct orientations of the ester groups relative to the triterpene backbone. Moreover, comparison of the self-assembly modes of GE esters in their unsolvated forms with the supramolecular organization of GE and carbenoxolone in their solvated crystals revealed that ester substituents replace solvent molecules hydrogen bonded to the COOH group at the triterpene skeleton, resulting in similar packing arrangements of these compounds.

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Section: Ester Derivatives Of Ge -Comparison Of Crystal Packingmentioning

confidence: 78%

Section: Introductionmentioning

confidence: 84%

Self-assembly modes of glycyrrhetinic acid esters in view of the crystal packing of related triterpene molecules

Langer

Wicher

Szczołko

et al. 2016

Acta Crystallogr B Struct Sci Cryst Eng Mater

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“…In line with in vitro experiments, different tumor-bearing rodent models have also indicated the inhibitory effects on tumor growth of this CO donor [ 63 , 65 , [68] , [69] , [70] , [71] ]. Besides, a variety of novel CO-RMs have been designed and synthesized successfully, which have showed similar anticancer actions in both in vitro studies [ [72] , [73] , [74] , [75] , [76] , [77] , [78] , [79] , [80] ] and in vivo experiments [ 65 , 69 , 79 ]. In contrast, an in vitro study using human hepatocellular carcinoma cell lines showed that cell cycle arrest was attenuated by the pretreatment with CORM-2, interrupting the inhibition of cancer cell growth [ 81 ].…”

Section: Anticancer Activities Of Co-rms By Targeting Cancer Hallmarksmentioning

confidence: 99%

The potentials of carbon monoxide-releasing molecules in cancer treatment: An outlook from ROS biology and medicine

Tuan

et al. 2021

Redox Biology

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Carbon monoxide (CO) is now well recognized a pivotal endogenous signaling molecule in mammalian lives. The proof-of-concept employing chemical carriers of exogenous CO as prodrugs for CO release, also known as CO-releasing molecules (CO-RMs), has been appreciated. The major advantage of CO-RMs is that they are able to deliver CO to the target sites in a controlled manner. There is an increasing body of experimental studies suggesting the therapeutic potentials of CO and CO-RMs in different cancer models. This review firstly presents a short but crucial view concerning the characteristics of CO and CO-RMs. Then, the anticancer activities of CO-RMs that target many cancer hallmarks, mainly proliferation, apoptosis, angiogenesis, and invasion and metastasis, are discussed. However, their anticancer activities are varying and cell-type specific. The aerobic metabolism of molecular oxygen inevitably generates various oxygen-containing reactive metabolites termed reactive oxygen species (ROS) which play important roles in both physiology and pathophysiology. Although ROS act as a double-edged sword in cancer, both sides of which may potentially have been exploited for therapeutic benefits. The main focus of the present review is thus to identify the possible signaling network by which CO-RMs can exert their anticancer actions, where ROS play the central role. Another important issue concerning the potential effect of CO-RMs on the aerobic glycolysis (the Warburg effect) which is a feature of cancer metabolic reprogramming is given before the conclusion with future prospects on the challenges of developing CO-RMs into clinically pharmaceutical candidates in cancer therapy.

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“…Among them, complex 3 was the most potent, with an IC 50 of 37.22 μ M [ 32 ]. Interesting are also the relatively slow CO-releasing cobalt-containing CORMs ( Figure 3(D) ) designed by Gong et al [ 33 ]. Appropriate MTT assays showed that the slow CO-releasing CORMs could inhibit the proliferation of HeLa cells with IC 50 s less than 120 μ M, reflecting their potential anticancer activity.…”

Section: Corms and Cancer Therapymentioning

confidence: 99%

“…Finally, the authors proved that these complexes could block cell cycle in the G2/M phase, inhibiting division and proliferation, and increasing intracellular reactive oxygen species (ROS) concentration, possibly through CO and cobalt ions released after CO loss. Hence, they hypothesised that the antiproliferative activity of the synthesised compounds resulted from the binding of CO to proteins of the mitochondrial electron transfer chain leading to an intracellular ROS level increase, as well as the release of cobalt species that can bind to endogenous substrates interrupting cell cycle and provoking apoptosis [ 33 ].…”

Section: Corms and Cancer Therapymentioning

confidence: 99%

Aspects of Carbon Monoxide in Form of CO‐Releasing Molecules Used in Cancer Treatment: More Light on the Way

Kourti

Jiang

Cai

2017

Oxidative Medicine and Cellular Longevity

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Carbon monoxide (CO) has always been recognised as a toxic gas, due to its higher affinity for haemoglobin than oxygen. However, biological studies have revealed an intriguing role for CO as an endogenous signalling molecule, a gasotransmitter. CO is demonstrated to exert many cellular activities including anti-inflammatory, antiapoptotic, and antiproliferative activities. In animal studies, CO gas administration can prevent tissues from hypoxia or ischemic-reperfusion injury. As a result, there are a plethora of reports dealing with the biological applications of CO and CO-releasing molecules (CORMs) in inflammatory and vascular diseases. CORMs have already been tested as a therapeutic agent in clinical trials. More recently, an increased interest has been drawn to CO's potential use as an anticancer agent. In this review, we will aim to give an overview of the research focused on the role of CO and CORMs in different types of cancer and expand to the recent development of the next generation CORMs for clinical application in cancer treatment.

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Synthesis, toxicities and cell proliferation inhibition of CO-releasing molecules containing cobalt

Cited by 17 publications

References 30 publications

Self-assembly modes of glycyrrhetinic acid esters in view of the crystal packing of related triterpene molecules

Self-assembly modes of glycyrrhetinic acid esters in view of the crystal packing of related triterpene molecules

The potentials of carbon monoxide-releasing molecules in cancer treatment: An outlook from ROS biology and medicine

Aspects of Carbon Monoxide in Form of CO‐Releasing Molecules Used in Cancer Treatment: More Light on the Way

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